I'll start the replys...
I guess you have to decide if any of the things he talked about are something you can not handle, or have a moral problem with. For me if he was a nice guy I would probably go out with him again.
I have no problem with gamblng (even large sums), but I would hope that he uses the philosphy that he only takes what he can afford to lose. Being a Health Teacher as you previously mentioned $6000 sounds like a lot, but we don't know anything about the rest of his finances...
As far as the wild and crazy things, we've all been there done that. Some of us just more than others
I personally am pretty liberal when it comes to things like that - especially if they were in the past, so I would probably have been right there laughing along with the stories
Hope I helped.
Edited to add: that of course if he has a gambling problem (read: beyond his means, can't pay rent, has to borrow to live) then definitely run very far and fast!